1-丁-2-烯-2-基-2-硝基苯 | 60249-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-丁-2-烯-2-基-2-硝基苯
• 英文名称: 1-(1-methyl-propenyl)-2-nitro-benzene
• 英文别名: 1-(But-2-en-2-yl)-2-nitrobenzene；1-but-2-en-2-yl-2-nitrobenzene
• CAS: 60249-96-9
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: GRRALLGDUKCJIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-丁-2-烯-2-基-2-硝基苯 在 palladium diacetate 一氧化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 21.5h， 以97%的产率得到2,3-二甲基吲哚
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of Indoles by Reductive N-Heteroannulation of 2-Nitrostyrenes

  摘要：

  A palladium-phosphine catalyzed reductive N-heteroannulation of 2-nitrostyrenes, in the presence of carbon monoxide, producing indoles has been developed. Indoles were obtained, in moderate to excellent yield, from substituted 2-nitrostyrenes having either electron-withdrawing (NO2 and CO2Me) or electron-donating (Br, OH, Me, OMe, and OTf) substituents on the aromatic ring. Best results were obtained using palladium diacetate (6 mol %) together with triphenylphosphine (24 mol %) as the catalytic system, under 4 atm of carbon monoxide in acetonitrile at 70 degrees C. Other palladium(II) and palladium(0) complexes also catalyze the reaction.

  DOI：

  10.1021/jo970516+

文献信息

• Palladium-Catalyzed Synthesis of Indoles by Reductive <i>N</i>-Heteroannulation of 2-Nitrostyrenes
  作者：Björn C. Söderberg、James A. Shriver

  DOI：10.1021/jo970516+

  日期：1997.8.1

  A palladium-phosphine catalyzed reductive N-heteroannulation of 2-nitrostyrenes, in the presence of carbon monoxide, producing indoles has been developed. Indoles were obtained, in moderate to excellent yield, from substituted 2-nitrostyrenes having either electron-withdrawing (NO2 and CO2Me) or electron-donating (Br, OH, Me, OMe, and OTf) substituents on the aromatic ring. Best results were obtained using palladium diacetate (6 mol %) together with triphenylphosphine (24 mol %) as the catalytic system, under 4 atm of carbon monoxide in acetonitrile at 70 degrees C. Other palladium(II) and palladium(0) complexes also catalyze the reaction.
• Shabarov,Yu.S. et al., Journal of Organic Chemistry USSR (English Translation), 1976, vol. 12, p. 1289 - 1292
  作者：Shabarov,Yu.S. et al.

  DOI：——

  日期：——
• SYNTHESIS OF INDOLES BY PALLADIUM-CATALYZED REDUCTIVE N-HETEROANNULATION OF 2-NITROSTYRENES: METHYL INDOLE-4-CARBOXYLATE
  作者：Söderberg, Björn C.、Shriver, James A.、Wallace, Jeffery M.、Warren, J. David、Hegedus, Louis S.

  DOI：10.15227/orgsyn.080.0075

  日期：——